Perylenes Bearing Multiple H-Bonding Donor and Acceptor Groups for Photonic Applications

Construction of supra-molecular self-assembled building blocks due to their relevance in organic, inorganic, polymeric compounds as well as biological systems has attracted many attentions and various well-defined supra complexes with different sizes and shapes in the range of 1-100 nm dimensions have been prepared. Modification of perylene dye at imides or bay positions leads to high solubility of the product along with wide range of absorption expands to near infrared region. In the present study, Three different perylene diimide which two of them were symmetrical (N,N'-bis-[2-(5-carboxamidyl-3-cyano-4-methyl)-thienyl]-3,4,9,10-perylene bis (dicarboximide) TPDI and N,N'-bis-[3-((2-methyl-5-pyrimidinyl) methyl)-5-(2-hydroxyethyl)-4-methylthiazolium] perylene-3,4:9,10-tetracarboxylic diimide TCPDI and one was highly soluble asymmetrical (N-(dehydroabietyl)-N'-[3-((2-methyl-5-pyrimidinyl) methyl)-5-(2-hydroxyethyl)-4-methylthiazolium] perylene-3,4,9,10-tetracarboxylic diimide TAPDI with donor-acceptor-donor (DAD systems) building block have been synthesized, in order to change the photophysical and photochemical properties of the diimides, 1,7-symmetrically substituted perylenebis (dicarboximide) dyes (N,N'-di((s)-1-phenylethyl)-1,7-di(3,5-diamino-pyrimidoxyl) perylene-3,4,9,10-tetracarboxy diimide BPY-PPDI, N,N'-bis-[3-((2-methyl-5-pyrimidinyl) methyl)-5-(2-hydroxyethyl)-4-methylthiazolium]-1,7-di-(2-[3[(4-amino-2-methylpyrimidin-5-yl) methyl]-4-methyl-1,3-thiazol-3-ium-5yl] ethoxy-perylene-3,4:9,10-tetracarboxylic diimide BTC-TCPDI and N,N'-bis-(dehydroabietyl)-1,7-di-(2-[3[(4-amino-2-methylpyrimidin-5-yl) methyl]-4-methyl-1,3-thiazol-3-ium-5-yl] ethoxyperylene-3,4:9,10-tetracarboxylic diimide TC-APDI with electron donating groups have been synthesized in good amount of product under mild conditions, The products have been purified and optical, thermal and electrochemical properties of them were measured and characterized carefully. Keywords: Perylene, thiophene, vitamin, bay-substitution, hydrogen bonding.